What Jon Stewart and The Daily Show can teach you about managing your time

I met Jon Stewart once. He and the head writer of The Onion were promoting their new book, America (The Book): A Citizen’s Guide to Democracy Inaction, at Poets and Prose in Washington, DC. Now, this was before Aasif Mandvi and Hasan Minhaj became correspondents, and I had a plan to pitch him on a totally great idea that they needed an South Asian American correspondent (me). I had a sketch written out and ready to perform, which I’d go into detail here but then we’d wade into solidly political territory on our product management blog. All you need to know is that it was great.

I approached Jon full of confidence and ready to deliver. Here’s what I happened:

Obviously, I crushed it. I may not have made it in front of the camera, but Jon clearly got the point. Aasif and Hasan owe me. In any case, like so many, I’m a fan of the show.

. . .

A while back, Jon sat down with Terry Gross for an episode of Fresh Air and gave some fascinating insight into how they go about making the show. It’s incredible when you think about it. They have to go through hundreds of hours of televised news, create a few narrative threads, write the jokes, rewrite, rehearse, and then tape in front of a live audience every day, four days a week. And they do it all by the same time every day because Comedy Central isn’t waiting around for them to finish. The ultimate timebox.

Jon explains a pretty regimented process that he admits people might find pretty boring. “People think we’re just sitting around telling jokes all day, and that’s not the case.” They go through a morning meeting and an afternoon meeting with 2 phases of writing in between. I’ve long had debates with people about creative freedom, and Jon says something that really sticks out for me.

“I’m a real believer in that creativity comes from limits, not freedom. Freedom, I think, you don’t know what to do with yourself. But when you have a structure, then you can improvise off it and feel confident enough to kind of come back to that.”

I’ve found this to be true whether it’s writing a story, practicing a presentation, running a brainstorming session, or putting a project plan together. In fact, I used to (briefly) write for a sketch comedy team, and we were given assignments to do in 15 minutes. 15 minutes does not sound like a lot of time, but somehow, almost every time, we’d pull it off. I’m not sure I can explain the dynamics of why it kept working but Jon’s words ring true.

At the end of 15 minutes, we had to read our sketches out loud to the group, which was pretty damn nerve-wracking. The way it usually worked was that we would spin in our heads for a few minutes while everyone just anxiously stared at a blank piece of paper. But as the time limit approached, images started forming in our heads, words formed, sentences formed, and before we knew it, we all had sketches worked out. We all kind worked out our own structure. They weren’t always great, but every now and then, we struck gold.

Bringing this into work, I’ve found that when I don’t budget time for specific tasks particularly the smaller ones, they don’t get done. Free time on my calendar is often when I spin without a goal, and I later wonder why something I intended to get done didn’t get done by the end of the day. It’s easy to be overwhelmed by the many big things we need to do and pass on the smaller, essential tasks we need to accomplish for our work.

For tasks that I need to do consistently such as coming up with new content, I set up weekly blocks of time. I don’t just call it “focus time” or “content,” I like to label them with a goal, such as “Create 5 ideas for new posts.” This label reminds me where I need to be at the end of that block of time. It can sometimes be hard to stick to a goal if there isn’t really an external pressure to get it done (no one is telling me to come up with 5 new ideas each week). But I’ve found that as I stick to it, it becomes more natural to adhere to these goals as I develop a rhythm and structure by doing them over and over again.

Additionally, if I need to read some books for research, I block off time for that on my calendar as well. Some people also block time for general tasks, such as “respond to Inbox.” This is also a great way to make sure that tasks you’re always doing, such as checking email, don’t interfere with the work you need to focus on. To connect these tasks to your broader objectives, check out what we wrote about defining objectives.

The point of this is to fill up your calendar with the things you need to get done. This isn’t to “appear busy”, but to properly allocate your time to do the tasks you need to do. The reality of your job and life means you’ll need to adjust accordingly, but as Jon said, you can feel confident enough in your planned time to come back to it.

. . .

So my time limit to finish this post is ending. If you’re not convinced about my sketch writing anecdote, I invite you to try it out for yourself!

Put a 15 minute block on your calendar like “share an article with 5 friends.” It can be a blog post or an email. At the end of the 15 minutes, you’ve got to send it to them. So at the beginning, start thinking about what you’ll write and then start writing.

Here’s the writing prompt: Describe a time something happened that you didn’t expect at all and were pleasantly surprised. Have fun!